


You Want To Play A Game Of What?

by JamieMac26



Category: Dylan O'Brien - Fandom, Teen Wolf (TV) RPF
Genre: Explicit Language, F/M
Language: English
Status: Completed
Published: 2016-08-07
Updated: 2016-08-07
Packaged: 2018-08-07 07:03:33
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 5,029
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7704988
Author URL: https://archiveofourown.org/users/JamieMac26/pseuds/JamieMac26
Summary: <blockquote class="userstuff">
              <p>“Oh, you so need to back up that statement. What would you say to a little wager?”</p><p>Madison Woodley had been friends with Dylan O'Brien for several years, but a bet made during a night out leads to so much more than she ever expected.</p>
            </blockquote>





	You Want To Play A Game Of What?

The bar was dark. Music pulsed through the floorboards and reverberated off the walls. It was still fairly early, so there were not too many bodies filling the space quite yet.  I spied two empty tables near the rear, in a darkened corner.  I pointed in that direction, signaling to the couple friends with me, where we needed to head. After procuring the tables and ordering a couple pitchers of beer, I worked my way towards the restrooms on the other side of the room. I washed my hands and touched up my makeup. After applying some much needed lipgloss, I pulled my phone out of my purse to check on the status of the rest of our party.  I smiled as I read the message that they had arrived and I exited the quiet of the bathroom, entering the hoard that had magically appeared in the now not-so-quiet bar. 

As I approached my group of friends, I rolled my eyes when I noticed someone sitting in my already claimed seat. “Seriously O’Brien, do you purposefully try and irritate me?”

His head whipped around and he glared at me, “What the hell are you talking about?”

“You are sitting in my seat,” My hands automatically went to my hips.

“Whatever, Woodley! Your name wasn’t etched in the fucking chair, so walk away.” He waved his hand at me, laughing as he motioned for me to move away from him.

Instead, I pulled the chair next to him out, perching myself on the edge of the stool. I leaned in towards him, “Pour me a glass, please.”

He did as I asked and slide it in my direction, “You just can’t stay away from me, can you?” He winked, the grin on his face broadening. 

“What can I say Dylan, you’re irresistible,” I said as I rolled my eyes.

“Damn straight I am, and don’t you forget it,” He clinked his glass against mine. 

I chuckled softly, “Oh O’Brien, it must feel good to have that much confidence.”

He eyed me carefully, his gaze scanning my body, “Just admit it Mads, you want all of this. “ He made a grand gesture at himself and I nearly spit out my beer.

“You’re right,” I held my glass up to my lips and smirked in his direction. 

He was then pulled into a discussion with the other men at our tables and I watched as he went back to his conversation with Tyler. There was something about Dylan that intrigued me. I loved the back and forth banter that would always occur between us. His sarcasm and wit were always spot on and he was one of the few guys that could keep me on my toes, all the time. The fact that he was extremely attractive being an added bonus. We had been friends, or at least had the same group of friends for a couple years now, but Dylan and I had never hung out together, just us. I wanted that to happen and I had wanted that to happen for several months now. It just all came down to the how. The conversation soon turned towards the topic of sports, a topic I could hold my own in. However, they were once again talking baseball, which wasn’t really my favorite sport, but being around Dylan and Tyler, I’ve learned a few things. 

“I could strike you out man, I’m not even sure it would be that hard,” I heard Dylan smack talk one of the other men sitting at our table. I grinned, knowing that I had my opening. 

I put both elbows up on the table, my arm brushing against Dylan’s, “What about me, could you strike me out?” I batted my lashes at him, leaning in even closer.

He took a slow sip of beer, before ducking his head down, his lips a mere wisp away from mine, “Now that would be easy.”

“Hmmm,” I lowered my arm, the one closest to his body, below the table, and ghosted my fingers along his thigh. I heard his breath hitch and he glanced down at the tabletop, “Would it really be that easy?”

He nodded his head as I placed my hand, palm down, on his thigh, and slowly worked it towards the inside of his leg. I licked my lips seductively, his eyes glued to my face as I made the slight gesture.

He seemed to gain composure, closing his eyes for a moment, “Yep, I do think it would really be that easy. What do you even know about baseball, or for that matter, when was the last time you played or held a bat?”

I laughed at his string of questions, “Details, details… I grew up playing sports Dylan, swinging a stupid bat would be easy peasy.”

“Oh, you so need to back up that statement,” He reached for the pitcher, refilling my glass along with his. “What would you say to a little wager?”

Our entire table had grown quiet, watching the interaction between me and Dylan. The noise in the bar made it so I had to lean in even closer to him to hear what he had to purpose. “I’m game, what do you have in mind?”

He rubbed the beard covering his chin as he kept his brown eyes on me, “A little test of skill with a twist, a game of baseball horse.”

“Baseball horse? Did you just make that shit up?” 

He nodded his head, “We go until one of us loses. If you hit one of my pitches, I get a letter, but everytime I hit three of your pitches in a row, you get a letter. We go three by three and the first one to HORSE loses.”

“I know how the game is played O’Brien, what is the wager?”

Again he rubbed his chin, taking his eyes off me for the first time since this conversation had started, “If I win, you agree to go out on a date with me.”

“And if I win,” I did my best to hide my excitement at the prospect of not only spending some time alone with Dylan, but possibly going on a date with him as well.

“Name your price,” He took a slow drink of the amber liquid.

I took his moment of silence to figure out what I wanted. Going out with him was already on the table, and to be honest, that was the only thing I desired, but I needed to come up with something, or I would seem too eager. “Tyler,” I shouted for my friend’s attention. 

“Yo,” He leaned around Dylan and looked over at me.

“You still want to hit up that karaoke place?”

“Hell ya,” He shouted.

I looked back at Dylan, “If I win, you join me and Tyler for karaoke humiliation.”

“Seriously, that’s what you want?” 

I nodded my head, “Yeah. I think it would be rather entertaining and I hear that you’re quite the karaoke professional.”

He chuckled, “I’ve been known to throw down a song or two from time to time, but you realize that it isn’t humiliating for me, right?”

I just shrugged my shoulders, “I couldn’t think of anything else.”

He licked his lips, just as I had earlier, and that simple movement had me squirming in my seat. 

“You could always hold off, wait and see if you actually win first, then come up with what you want.” He scooted his stool away from the table, standing up and extending his hand towards me. “There is a field near my house, let’s go and see if you’re really as good as you claim to be.”

I hadn’t expected it to be right now, but I took his hand and hopped down.

“Good luck Madison! You are going to need it,” Tyler’s lack of confidence hit my ears as I turned around and waved goodbye to our friends. 

Thankfully I had caught a ride to the bar with a couple other people, so the decision on who’s car to take came down to just his. I jumped up into the dark sedan and buckled up while he shut my door. I grinned at the gentleman-like behavior. 

“We have to make a quick stop at my house first to grab the gear,” He stated as he started the car.

I laughed, “You mean to tell me that you don’t carry about bats and balls in the trunk of your car at all times.”

“Hmmm.. shockingly, no,” His laughter echoed along with mine in the confines of the small space. 

Sitting in silence as we drove towards his house was gnawing slowly at my nerves. I felt raw but I had a nervous tingling flowing through me. Being this close to Dylan and this alone with him was overwhelming all of my sensations. He hummed along quietly to the radio, bobbing his head to the steady beat.  I couldn’t keep my eyes off of him, though I didn’t want to stare, I was finding it harder and harder to hide my actions. I watched as he stole a glance in my direction, his eyes and lips smiling at me, a wink shortly following suit. My stomach flipped somersaults and I squirmed slightly in my seat. 

“So,” He stated quietly, “How come we’ve never hung out before? Just the two of us?”

I shrugged my shoulders, “I guess the opportunity has never presented itself before now.”

“I’m glad that it’s finally decided to show up,” He said as he threw a cocky grin in my direction.

I shook my head and giggled, “So how far is this field from your house?”

“Around the corner, literally. We could actually just walk there, but wait, we’ll need the headlights from the car to be able to see what we’re hitting.”

“Oh, good thinking O’Brien! I wouldn’t want to mar that beautiful face of yours with one of my impressive….” I stopped, my cheeks suddenly on fire. “Oh shit, Dylan...I am so sorry. I didn’t mean anything by it, I swear.” The warmth of his hand on mine, silenced my rambling apology. I glanced over at him but his eyes were glued to the road. 

“Madison, it’s okay.”

His voice was a tad huskier than normal, and my anxiety level steadily rose. “Dylan,” I started, but he gave my hand a squeeze, once again causing me to stop speaking. 

This time, he turned his head to look at me, “Just stop apologizing, I know.” 

His hand stayed, gripping mine tightly and I felt my heart-rate slowly beat back to normal. Dylan’s accident had taken place months ago, but the full beard that he now donned kept the evidence hidden, and I had allowed myself to forget. We didn’t talk about it, none of us did. We were all just thankful to still have him with us, we didn’t feel a need to hash out the details. 

The car slowed as he spun the wheel to the right. A large gate was illuminated in the headlights and Dylan stopped, punching in some numbers on a small electronic keypad.  The gate silently opened, allowing us access to the darkened road ahead. I stared at the homes as we passed them, one by one. Dylan lived in a modest neighborhood, exactly what I would have expected from him. He made another right turn before easing the car onto a concrete driveway. The night was brightened by the light from the opening garage. 

He placed the car in park and opened his door, turning to glance my way, “Come help me.”

I followed his move, exiting the car and moving towards the corner of the organized space. Inside one of the many cupboards, he exposed an array of bats and balls, mitts and empty bags. He picked up one the bags, handing it to me, before turning back around and grabbing a hold of a couple bats and several baseballs. He stuffed them into the open bag in my hands, picking up two mitts before zipping up the duffle and taking it from me. He smirked at me and proceeded to make his way back towards the awaiting car. 

 

He was right, the ballpark was only a handful of blocks away and it was dark and completely deserted. He angled the car so the headlights shined brightly past home plate towards the pitcher's mound.

“Doesn’t this make it hard for the person throwing the ball,” I questioned as I dumped the mitts next to the bag he’d dropped on the ground.

He shook his head, “Maybe a little, but I’m not sure how else we’d light it up enough to be able to see. It’s not like I can pull the car out onto the field.” 

He bent down to unzip the bag and I couldn’t keep my eyes off his backside. His jeans tightened in all the right places and an instantaneous warmth flooded my stomach. I turned my body, so that I was staring off into the inky blackness of the outfield

“Here…”

I turned at the sound of his voice, just in time to catch a baseball, stopping it from hitting me in the chest. “You want me to go first?”

He nodded, taking a couple practice swings with the bat that he held in his large hands, “You were the one running her mouth at the bar, so let’s see what you’ve got Woodley.”

I stuck my tongue out at him, spinning on my heel and sauntering to the mound. I looked down at my hands, the small white ball gleamed in the glow of the headlights. As I pictured throwing it in Dylan’s direction, I was struck with an idea of inspiration. I turned and faced him, his ballcap was perched backwards on his head, and my heart skipped another beat. “I want to up the ante.”

He spun the bat in his hands, “And what did you have in mind?”

“We need to make this game a little spicey.  We’re the only ones here, so how about with every letter, we lose an article of clothing?”

He blinked, licking his lips slowly, “Strip HORSE?”

I cocked my head to the side, resting it on my shoulder, a sly grin forming on my lips, “What do you say O’Brien, still think you can beat me?”

“Oh Madison, you have no idea what you’ve unleashed. Now throw that damn ball!” 

I watched as he took his stance at home plate, his hips wiggling as he dug his heels into the dirt.  He took a couple practice swings, before nodding in my direction. I took a deep breath, grasping the ball tightly, I brought my arm backwards, behind my head. I glanced once more at Dylan, before reeling my arm forward, releasing the ball at just the right moment. I watched as it flew towards the man standing a few feet in front of me. I watched as he swung, the sound of the bat impacting with the ball, cracking in the still night air, watching as it flew past me, disappearing into the shadows. I inwardly groaned, knowing that only two more hits, and I would be the first one to start stripping. 

Dylan tossed me another ball, “You gotta do better than that if you want to beat me at my own game Woodley.”

“Wow, already gloating and we’ve only just started. That was just a warm-up O’Brien, I’ve got a little something something up my sleeve.” I spun on the mound quickly, trying to catch him off guard as I released the ball. Unfortunately, he was quicker or had been expecting my little diversion, for once again, the sound of the metal singing echoed in my ears. “Damnit Dylan!”

He laughed, tossing me one more ball, “If that was your ‘something something’ you are going down so hard.”

“Oh, I will make you hard Dylan, and that will be easy,” I winked at him, throwing the ball, one last time. I grimaced, my head hanging, as I watched him hit the last ball. 

“Oh, I have no doubt that you can and will, but for now, strip,” Dylan motioned at me with his bat.

His eyes were on me as I toed off my sandals, picking them up and tossing them off to the side. 

“What?” He stated, shocked, “That’s not fair!”

I shrugged, making my way towards him, “We never specified which articles of clothing counted. I think it’s my turn now, give me that.” I pulled the bat from his hands, nudging him with it. “I think that your place is over there.”

“Oh, is that how you want to play this? Cheaters never win Madison,” He jogged out into the field, retrieving the balls he had hit. “You get three chances, you ready for this?”

I nodded my head, taking a couple practice swings of my own. My bare feet were already coated in dirt, but I smiled at the thought of Dylan standing on that mound in nothing but his boxer-briefs.

“What are you grinning at? You haven’t won this thing yet. Are you ready?” He tossed the ball up and down, the small object disappearing beneath his long fingers.

“Just having colorful images of you standing up there, mostly naked,” I threw him a sultry look, licking my lips, “I’m ready when you are.”

My words threw him for a second, but he regained composure and threw the ball, quickly, in my direction. I kept my eyes on it, swinging at what I thought was the right moment, but the sound of the ball hitting the chainlink behind me, told me all I needed to know.

“Two more chances Woodley, you sure you want to keep going?”

“Oh for god’s sake Dylan, shut up and throw the damn ball,” I held the bat at the ready again, waiting for his next pitch.

He chuckled wholeheartedly, once again throwing the ball. I swung, missing once more. 

“Ugh,” I hammered the bat into the soft earth, “Again, again.”

“You realize that if you don’t hit this, you have to take off another item...this time,” He stopped, scratching his chin, “This time you lose your shirt.”

“Wait, you don’t get to decide what I have to take off, that wasn’t part of the rules.”

“New rule. My game, my rules.” He threw the ball, catching me off guard.

I swung, missing yet again. I narrowed my gaze at his laughing figure. 

“The shirt Madison, needs to come off,” He wiggled his fingers at me.

I rolled my eyes, grabbing at the hem of my shirt and tugging it up over my head. I tossed it over my shoulder, near where my shoes sat. It was a good thing I decided to wear my cute underwear tonight. The bright pink fabric and lace seemed almost neon in the glaring lights of the car. “There, are you happy now?” 

His tongue was held in place by his lips and teeth, his eyes scanning my chest. He nodded his head slowly, “Oh yeah, very happy. I like the pink, it suits you.”

“You are a horrible human being O’Brien, and you will be paying for this. Go and get the balls, please.” I crossed my arms underneath my breasts, pushing them up, giving him a better view. Two could play at this game.

He stared a moment longer before turning around and gathering up the baseballs. He jogged back to the pitcher’s mound, depositing all three in my arms. “So far, I’ve got you by two letters...you sure you want to keep playing?”

I pointed at home plate, not speaking a word. He laughed, turning back around and picking up the discarded bat. “Give me your best effort there Woodley.”

I threw the ball as hard as I could, my boob almost popping out from the effort, however, that small chance at exposure was enough to distract Dylan, and he missed the ball by a mile. I jumped up and down, holding my chest for safety, “Ha, I want the pants gone boy!”

“Seriously, you go straight for the goods,” He popped the button, slowly lowering the zipper. 

“You’re one to talk,” I pointed at the girls.

“You should not be ashamed. You have very nice tits.” He pushed his jeans down his thighs, past his calfs, and with one hand on the fence, extracted them off his legs. 

A grin broke on my face as I watched him free himself from the denim, “I told you I could get you hard.”

He glanced down, the bulge evident, “What? Stop staring. This has nothing to do with you.”

“Sure, like I believe that. Now, I think that it’s my turn.” I crossed the short distance, reaching over to pick up the bat he’d dropped. I stood up, inching my way closer to him, my body nearing his. I brushed my hand against his arm, my leg making contact with his now bare one. “You sure it has nothing to do with me?”

He glanced down again, his cheeks turning a slight shade of pink, “You are evil.”

He trotted by me, making his way out to the mound. I took a couple practice swings, making sure that he got a full view of the motion of my chest. 

 

Several turns later and I was perched back on the pitcher’s mound, donned only in my bra and panties. “You’ve still got your hat on.”

“Yeah, so? How does my hat count?” He pulled it off, pushing his hair back, repositioning it again. 

I motioned the length of my body, “You’ve made sure that I’m in nothing but my skivvies, so I think you need to match.”

“I’d prefer to have you in less, but you won’t do it.” 

“Well,” I pointed out towards the black outfield, “How do I know that there aren’t some pervy kids out there watching us.”

“Pervy kids huh,” He laughed.

I placed my hands on my hips, “Fine, disgusting old men or…” I turned around and peered into the dark, “Maybe some of your female fans lying in wait for the moment that I get you out of those boxer briefs.”

“Don’t use my fans as an excuse, I know that you’re dying to get me out of these,” He snapped the waistband of his underwear against his flat stomach and I couldn’t stop my jaw from dropping.

My eyes followed the trail of hair as it disappeared beneath the material, “I can’t disagree with you.”

He kept his eyes on my body as he slowly walked towards me, “I’m all for taking this little stripping adventure back to my place.”

His arms snaked around my bare waist and I placed my hands flat against his chest, “O’Brien, I’m so not the kind of girl that just jumps into bed, I need to be wooed.” I danced my fingertips along his shoulders, tracing the lines of his muscles as I slide them down his arms. 

“I can woo, I can woo hardcore. What kind of wooing are you thinking about?” He pulled me closer to him, his arms tightening around me. 

“Hmmmm….” I leaned forward, pressing my lips to his neck, the vibration of my reply causing a soft moan to escape him. 

“Madison…”

I felt him shiver as I ghosted my lips across his adam’s apple, then up along his jawline.

“Madison…” He tried speaking again, his words sticking in his throat.

“Having a hard time forming a sentence Dylan,” I giggled, knowing what my light touch was doing to him, as I could feel it against my lower abdomen. 

He grabbed my hands, pushing my arms down to my side and holding me a step away from him, “If you keep doing that, I’m not going to care who is watching because I will take you right here.” He took a deep breath, his eyes fluttered closed.

“I don’t know about you, but I’m feeling awfully exposed right now...and well you,” I glanced down at the tent that had formed in his underwear, “I think we should probably call this a tie and put our clothes back on.”

“What? A tie??” He feigned surprise, his hand slapping against his bare chest, “I don’t think so Woodley! I won this bitch fair and square!!”

I laughed as I waltzed past him, heading towards the pile of clothes that had built up behind home plate, “If that’s the case, then I guess sex is completely off the table.”

“Whoa, wait a second,” He jogged after me, reaching the pile first, “I’ll give you the win, it’s all yours, just don’t take sex away from me.”

“Oh good god, you are such a guy…” I shook my head, reaching down to grab my shorts. “Do you really think I’d take that away? Hell, I’d be denying myself the pleasure as well.” 

I yelped out of surprise as he grabbed me from behind, spinning me around to face him. His lips descended upon mine and all of those questions that I once had about him being a good kisser, were answered with a resounding yes. I moaned and leaned into his body, my arms wrapping around his neck, my fingers intertwining themselves into the curls at the back of his head. He had one arm wrapped snuggly around my waist, and the other slid down my backside, his hand cupping my ass. I giggled into his lips at the thought of the situation I currently found myself in.  I had fantasies of kissing Dylan, of his hands all over me, of being able to know what he tasted like, what he smelled like, the feeling I would get being wrapped up against him. I groaned as he pulled away, putting a small distance between us. 

“Why are you laughing?” He pouted, his lips looking even more kissable.

“Because I’ve dreamed about this moment for so long, and the fact that it’s happening, while I’m standing in the middle of a baseball field, in the dark, in my underwear, just seems so surreal.”

“You’ve dreamed about us?” He face grew serious, his eyes almost black in the shadows cast by the headlights.

I nodded my head. For the first time tonight, I didn’t have any words, or at least I couldn’t make the words I wanted to say some out. I decided to use actions instead, and I closed the small gap, pressing my lips to his once again.

His warms hands roamed my mostly naked body, and I started to giggle again when his large palm covered one of my breasts. 

“Okay, you have got to stop doing that,” He mumbled against my lips and I could feel his smile.

“I’m sorry, it’s just...we have to look completely ridiculous and I really am feeling quite vulnerable.” 

His arms were around me again as he pulled me into his body.  He kissed the tip of my nose, then my lips softly, as he pulled back, staring into my eyes, “How about I take you home?”

I nodded, burying my head into the crook of his neck, taking in a deep breath, memorizing the feel of his skin against mine and the smell, slight hints of beer, smoke, dirt and sweat, that radiated off of him. 

We managed to finally get dressed, inbetween stolen kisses and touches, before loading up the car and heading in the direction of my apartment. I turned my body so that I was facing him, watching him as he studiously kept his eyes on the road. I reached forward, placing my smaller hand into his. “I had a really great time tonight Dylan, thank you for this.”

He nodded his head, bringing my hand up to his mouth, his lips brushing the back of it. He tucked our combined fists into his chest, and my heart started to beat just a little bit faster. A comfortable silence enveloped us and we rode in peace the rest of the way to my place. 

He moved the gear shift into park, reaching for the keys, but I leaned over and halted his movement. “If you walk me to my door, you won’t be going home tonight,” I playfully batted my lashes at him, “And as much as I want that, I want to see if this,” I pointed from myself to him, “Has a future.”

“Next Friday, I want to take you out.” 

“I was so hoping you’d say something like that,” I grinned as his hands cupped my cheeks, pulling me towards him. His lips were warm and as his tongue swept along my bottom lip, I parted, allowing him complete access.  The kiss intensified and I wanted his body pressed against mine again, but the console hampered that happening. Begrudgingly I pulled away, again, and gently removed his hands from my face. “Good-night Dylan,” I pushed the door open, turning to face him one last time, “Text me and I am really looking forward to what you’ve got planned for us next Friday.” I shut the door softly and started to head in the direction of my front porch when his voice brought me to standstill. 

“Madison,” His window was down, his head protruding from the car.

I walked over towards him, leaning down so my face was a breath away from his, “Yes O’Brien?”

His lips met mine again, the kiss eager and hungry and I smiled against them. 

“Just wanted to tell you to have a nice night,” He pulled away, watching as I slowly licked my lips. 

I waved at him as his car backed out of the driveway, and kept my eyes focused on his tail lights as they disappeared into the night. My fingers brushed against my lips, an euphoric smile danced across my face. I sucked my bottom lip between my teeth, sucking on it gently as I played the events of the night through my mind. Dylan had surprised me, making memories beyond my wildest imagination and I couldn’t wait to see what he would dream up for our first official date. 


End file.
